合成路线:The reaction of the secoandrostane dicarboxylic acid (I) with acetic anhydride,propionic anhydride or DCC in THF gives the corresponding anhydride (II),which is reduced with NaBH4,LiAlH4,LiAlH(t-BuO)3 or LiBHEt3 in DMF or THF to afford the target 2-oxaandrostane derivative.Alternatively,this synthesis can also be performed in a one pot reaction.Reaction of the seco diacid (I) with acetic or propionic anhydrides and further reduction with NaBH4 yields the target 2-oxaandrostane derivative,without isolation of the intermediate anhydride.
参考文献标题:New process for the synthesis of 17beta-hydroxy-17alpha-methyl-2-oxa-5alpha-androstane-3-one
文献作者:Tuba,Z.; Mah? S.; S醤ta,C.; Szes,J.; Ferenczi,K.; Horv醫h,P.; L醤cos,K.; Mester,T.; Trompler,? (Gedeon Richter Ltd.)
参考来源:EP 1189925; WO 0077025
合成路线:The bromination of 17beta-hydroxy-17alpha-methyl-5alpha-androstan-3-one (I) with Br2 in DMF gives the 2-bromo derivative (II),which is treated with LiCl and Li2CO3 in refluxing DMF to yield 17beta-hydroxy-17alpha-methyl-5alpha-androst-1-en-3-one (III) (1).The oxidative cleavage of (III) by means of Pb(OAc)4 and OsO4 in AcOH affords the seco steroid (IV),which is finally submitted to a reductive cyclization by means of NaBH4 and NaOH in water to provide the target 2-oxa steroid (1-3).
参考文献标题:17-Oxygenated-2-oxa-3-oxosteroids
文献作者:Pappo,R.(Pfizer Inc.)
参考来源:DE 1171425; GB 0968206
合成路线:The bromination of 17beta-hydroxy-17alpha-methyl-5alpha-androstan-3-one (I) with Br2 in DMF gives the 2-bromo derivative (II),which is treated with LiCl and Li2CO3 in refluxing DMF to yield 17beta-hydroxy-17alpha-methyl-5alpha-androst-1-en-3-one (III) (1).The oxidative cleavage of (III) by means of Pb(OAc)4 and OsO4 in AcOH affords the seco steroid (IV),which is finally submitted to a reductive cyclization by means of NaBH4 and NaOH in water to provide the target 2-oxa steroid (1-3).
参考文献标题:Optionally 17-alkylated 17-oxygenated-2-oxaandrostanes and intermediates
文献作者:Jung,C.; Pappo,R.(Pfizer Inc.)
参考来源:GB 0991497; US 3101349
合成路线:The bromination of 17beta-hydroxy-17alpha-methyl-5alpha-androstan-3-one (I) with Br2 in DMF gives the 2-bromo derivative (II),which is treated with LiCl and Li2CO3 in refluxing DMF to yield 17beta-hydroxy-17alpha-methyl-5alpha-androst-1-en-3-one (III) (1).The oxidative cleavage of (III) by means of Pb(OAc)4 and OsO4 in AcOH affords the seco steroid (IV),which is finally submitted to a reductive cyclization by means of NaBH4 and NaOH in water to provide the target 2-oxa steroid (1-3).
参考文献标题:17-Oxygenated oxa-steroids and intermediates thereto
文献作者:Pappo,R.(Pfizer Inc.)
参考来源:GB 970446; US 3128283
产品链接: CAS No. 53-39-4››